Lithium Hydroxide → (RS)-N-(4-cyano-benzyl)-2-ethoxy-malonamic acid

HRID 1828115Notes

Reaction equation

HRID 1828115 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([O:18][CH2:19][CH3:20])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)=[O:7])C.[Li+].[OH-]>CO.O.C1COCC1>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[CH:5]([O:18][CH2:19][CH3:20])[C:4]([OH:21])=[O:3])=[CH:15][CH:14]=1)#[N:17]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 69641469HCID 69641469, compound

Product 1

HCID 22064699(RS)-N-(4-cyano-benzyl)-2-ethoxy-malonamic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (RS)-N-(4-cyano-benzyl)-2-ethoxy-malonamic acid ethyl ester (1.97 g) and LiOH (285 mg) in MeOH (14 ml), H2O (7 ml) and THF (14 ml) was stirred 3 h at 60° C. The solvents were evaporated, EtOAc was added and it was washed with HCl 0.1 N, water and brine. The aqueous phases were extracted again with more EtOAc. The combined organic phases were dried (MgSO4) and the solvent was removed to yield (RS)-N-(4-cyano-benzyl)-2-ethoxy-malonamic acid, 1.53 g (86%); of white solid. MS 260.2 (100, [M+H]+), 277.2 (13, [M+NH4]+)

Workup

  1. customThe solvents were evaporated
  2. additionEtOAc was added
  3. washit was washed with HCl 0.1 N, water and brine
  4. extractionThe aqueous phases were extracted again with more EtOAc
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-98a9eab62cf548129def9128896d146b
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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